


Pretty Pets

by Genderhawt (Genderhawk)



Series: Genderhawt's Gender Thots [1]
Category: Critical Role (Web Series)
Genre: Anal Fingering, Anal Sex, BDSM, Blood Kink, Bondage, Crossdressing, Double Penetration, Face Slapping, Multi, Non-Human Genitalia, Nonbinary Character, Other, Pinching, Plot What Plot/Porn Without Plot, Praise Kink, Scratching, Trans Character, Vaginal Sex, rope, they wear dresses but it's not a humiliation or sissy thing
Language: English
Status: Completed
Published: 2019-10-14
Updated: 2019-10-14
Packaged: 2020-12-16 10:41:18
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 2,375
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/21034925
Author URL: https://archiveofourown.org/users/Genderhawk/pseuds/Genderhawt
Summary: Mollymauk and Caleb get prettied up and absolutely wrecked. Caleb is a pure subby boy and Mollymauk is a Smart-Assed Masochist who gets exactly what they deserve, and then some.  Caduceus is a giving Dom, tailoring the scene to the needs of his partners.





	Pretty Pets

**Author's Note:**

> I took a break from writing one fic to write another for the same fandom.

Their eyes met Caduceus’. Both of them had to look up to do so as they were shorter than the firbolg when standing, let alone when they were kneeling on the floor at his feet. Molly’s eyes were alight with excitement, his cheeks and neck were flushed a dark violet that complimented the plum of the hickies that scattered their way down his bare chest. Caleb’s eyes were dark and anxious, this was a new thing for him, but that didn’t say as much as the bright pink flush of his pale face or the way his currently unmarked skin rippled with goosebumps… Or the way his breath caught when Caduceus flashed him that lazy grin.

The human and the tiefling next to each other, pale white skin tinged pink next to the rich purples, his left hand in their right hand… It was such a picture and Caduceus wished for a moment that he could pause the scene to paint, but that moment passed when he heard whispers down by his knees. He had been distracted by his thoughts and Molly, his Molly, was about to start something. Caleb, good boy that he was, shook his head at the rapid whispering that came from Molly’s full lips.

“Now Mx. Molly, what do you have to say that I’m not supposed to hear?” Molly jumped, startled into momentary silence. But there wasn’t much that could keep them quiet for long and, when they started to reply, Caduceus shook his head and put a finger to his lips. “That mouth of yours will get you in trouble… Best to fix that...”

“I thought you liked my mouth” Teased the tiefling, a look from Caduceus made him shudder before adding “Sir” with more than enough tease to earn the quick slap across his face that came next. The smile never changed or left Caduceus’ face, even as he brought his hand against Molly’s other cheek.

This did wonderful things to Molly though, it was exactly what they wanted and what they had explicitly asked for a few hours before. They whimpered softly, tears forming in their eyes that they blinked away before sticking a forked tongue out at Caduceus with a wink and a suggestive, and effective, wiggle of their hips. 

Caleb watched, his cock hardening as Molly squeezed his hand harder with each slap. He let out a soft whine when Caduceus stepped away and turned his back on the two. 

“Shh pretty boy, shh...” Murmured the firbolg in answer, pleased at how eager the human looked when he turned around again. “I’m just fixing something up for Molly over there...” Molly’s eyes were already on the phallic gag in Caduceus’ big hands when Caleb noticed it, their mouth opened slightly as a reflex but then they snapped it shut again. Caduceus only shook his head and chuckled, low and deep, as he grabbed Molly’s face roughly in one hand and pressed the gag to their lips. “Open up” It was an order and Molly moaned softly through his still clenched teeth.

Resisting the urge to roll his eyes, he turned to Caleb “Go get the ropes, the clothespins, and… the dresses.” 

Caleb jumped to his feet with a nod and a “Yes Sir!” before hurrying to get everything listed. Meanwhile Caduceus had placed his large, booted foot between Molly’s legs. He pressed the toe of the leather boot up and into Molly’s cunt roughly as his fingers dug into their jaw, forcing their mouth open enough for him to slip the gag in. Molly was lost the moment the boot touched their heat, they rocked their hips hard and fast moaning through the gag that was being fastened around their head. 

Caleb tapped Caduceus on the elbow, two dresses draped over one arm along with a bundle of hempen ropes and in the other hand he held a drawstring bag that was heavy with the requested pins. 

Grabbing Molly by the chin, Caduceus guided them to their feet and then onto the bed. He took Caleb by the hand and guided him to the bed as well, although more gently. 

“Now, Caleb, would you be so kind as to clean up the mess that our lovely Mx. Molly has made?” Caduceus saw that Caleb’s eyes went to Molly’s exposed cunt, exposed because the tiefling had spread their legs quite prettily, and this time Caduceus didn’t bother trying not to roll his eyes. “I mean the mess on my boot” He corrected, gesturing down at the sticky mess on one of his boots. 

Caleb swallowed hard “Yes Sir” He dropped down the side of the bed and onto the floor, at Caduceus’ feet where he belonged, and began to clean the large boot with his tongue. As Caleb licked and kissed at his boot, Caduceus took a clamp from the little bag and examined it slowly as Molly watched. After a few long seconds, he put the pin back and selected a length of deep green rope that was woven through with golden thread that glittered in the flickering candle light. His movements were deft and purposeful and it wasn’t that he was restraining Molly exactly, although the rope that encased their tits did climb across their shoulders in a way that would keep their hands lower than their shoulders, he was decorating the flamboyantly colored and inked tiefling that he loved so much.

Caleb, for his part, could have polished Caduceus’ boot all night. He was happy enough to do anything that the firbolg desired, even while his cock ached with need. But soon enough he felt a big hand coil into his hair and pull him up enough to look into his face. 

“Your turn” Said the big firbolg as Caleb stood up to receive a harness in a deep red that matched the pattern across Mollymauk’s body with only a slight adjustment in the rope between his legs. As Caduceus tied Caleb and ignored Molly, they whined and moaned and rocked their hips trying in vain to increase the pressure between their legs. 

Once Caleb was fully tied, Caduceus turned to Molly and pulled him to his feet roughly and by the hair. The deep green dress that Molly picked out was the first one he picked up so it seemed that Molly, with spit dripping down their chin, would be the first to get dressed. The dress was simple enough to just slip on, silky and barely there for all that it reached to the floor, it had a slip up one side that went past their hip and a deep V-neck that would have met that slit had it curved in that direction instead of away. 

Caleb had, in a surprising turn of events, taken even longer to pick his dress. It was much more modest, it glittered with red crystals along the asymmetric hemline and at the neck which exposed none of the human man’s collarbone.. It was the obscene way that his cock tented the dress that made it immodest more than anything. 

The last step was their collars. Molly’s was black and covered in rhinestones that made up a rainbow while Caleb’s was a simple crafted and padded ring of black leather. Caleb was first this time, he knelt once more, without prompting, and Caduceus whispered praise as the collar was fastened around his neck. Molly didn’t put up much resistance, just a token push up against the hands on their shoulders pushing down, before they were on their knees as well and collared as well.

“Now Molly, can you behave?” Caduceus asked softly, grinning lopsidedly when Molly nodded in ernest. He removed the gag slowly and wiped away the line of spittle that ran down the tieflings chin. They nipped at his fingers, expecting another slap but instead earning a sharp pinch to the exposed flesh of their upper thigh. He leaned over and licked at the small bead of blood at had formed in the indent left by his nails before coming up to kiss Molly softly on the lips. It was a chaste-seeming kiss, closed mouths and no tongue or fondling, but the heat that burned through Molly knowing that behind the lips was the taste of his own blood was far from chaste.

Watching was good for Caleb, he was nervous and uncertain still, but it was even better for Caleb when Caduceus turned to him and pressed a soft kiss to his lips as well before sitting on the edge of the bed. 

“You two look so pretty tonight...” Molly started to open their mouth to interrupt Caduceus but Caduceus clapped a hand over their mouth and shook his head. Molly’s tongue flicked over the palm that covered their mouth but the firbolg didn’t seem to react. “Too bad I can’t take you out like this...” 

As he spoke he unbuckled his belt and slid his pants down just far enough to expose his massive member and cause both of his pretty pets to lick their lips. 

“Please...” they begged in unison, Caleb adding “Sir” to the end of his whispered request. Caduceus nodded and both of them dropped to their knees and, in a way that had to have been rehearsed, they planted soft kisses from the base of his shaft to the tip before kissing each other above the large phallus between them as their hands twined around the shaft. They explored each other’s lips as their hands fondled and stroked, picking up pace with the increased pace of Caduceus’ breathing until he reached down and slowed their hands to a stop. He’d calmed his breathing enough that when he spoke his voice was as calm as ever.

“Up.” Was the first order, and once it was obeyed he lifted Caleb’s gown up to reveal his erection before grabbing the human’s hand and guiding it down to Molly’s dripping cunt. “Look at how desperate you both are… Maybe I should leave you like this...” He spoke as if it were for himself, although in reality it was a deliberate word choice designed to elicit the very whines that he heard. 

He grabbed Molly by the hips, pulling them into position with one leg on either side of his lap and his nails digging into their plush purple curves. Their entrance rubbed against his cock and their tail whipped back and forth as Caduceus grasped Caleb and pulled him in behind the tiefling, the purple tail now wrapping around Caleb and pulling him closer. 

“I won’t leave you like this though, I wanna see how you look all tired out” The calm voice rasped a little, breath catching as Molly squirmed and rubbed their clit against his dick with a moan and a shudder. In one swift movement, Caduceus thrust upward and pushed Molly down filling them to bursting and making them nearly scream with mingled surprise and pleasure. And pain. But they liked it, had expressly asked for it even… On multiple occasions. 

Caleb’s cock twitched as Caduceus handed him the oil from the bedside table with a wink, this had been discussed too but it still surprised Molly when the oil slick finger pressed into them and they moaned as Caduceus pulled out slowly and teasingly until just his tip remained inside. Molly shuddered, Caleb added another finger and more oil, and Caduceus pulled the neck of Molly’s gown to the sides to expose their tits. Molly keened as Caduceus sucks one nipple between his teeth and bites down at the same time that Caleb pulled his fingers out and replaced them with the head of his cock. 

The noise that came next must have been from Molly, although Molly saw only stars and remembered no noise, as they were pushed down slowly but firmly. Two of the people that they loved the most had their cocks slowly filling them, deeper and fuller than ever before. They rocked their hips, moaned, shuddered, and whined in turn. They leaned forward, pressing their face into Caduceus’ furry chest as Caleb and Caduceus thrust into them slowly but firmly. 

Caduceus had one hand in Molly’s hair and the other on Caleb’s ass, pulling and guiding respectively as they picked up the pace. Molly was the first to come and they screamed when it happened, their slick gushed around Caduceus’ cock and matted the fur at the base. Caleb was about to pull out, to let Molly rest, but Caduceus kept his insistent guidance up throughout the orgasm and after. Caleb succumbed next, only moments after the tears began to flow from Molly’s eyes. These were good tears, as the human and the firbolg knew. Molly cried when they came, especially if they got their wish and were fucked silly even after they begged for it to stop. Caduceus chuckled as Molly’s tail whipped even faster through the air, moaning softly under the laughter as his calm began to be more facade than anything else. Something at the base of his cock expanded, knotting the firbolg to the tiefling as Caleb began to whimper and curse softly in Zemnien. Molly whimpered as well when Caleb finally pulled out, his semen dribbling down the purple thigh and mingling with Molly’s and Caduceus’ come. 

Molly came next, the pounding of their cunt got faster and faster as they twitched and writhed. Caleb’s nimble fingers pulled at and stroked their nipples with skill and experience, this time their scream was hoarse and ragged. It was also muffled by Caduceus’ hand covering their mouth and nose, making enough of a seal that their heart rate picked up but not so tight that there was no air flow, just long enough to excite and tease without much real risk. 

It was the tightening of Molly’s orgasmic contractions that pushed Caduceus over the edge, and the control over the very breath of his toy. He came hard, filling Molly even further with seed. As he relaxed and laid back he pulled Molly down on top of him and let Caleb fall to his side, he sighed happily. “This was… nice...” Molly and caleb nodded their agreement and the trio drifted off to sleep in one happy, sticky, pile of limbs.

**Author's Note:**

> YES they wear dresses, NO this is not sissification. The dress is because dresses are sexy.


End file.
